Thermal management is of great significance for human activities. Attaining thermal comfort not only requires thermal control of building's macroenvironment, but also additionally personal thermal regulation. Radiative cooling technologies are anticipated to effectively lower building energy utilization and provide optimal thermal comfort for individuals in hot weather. Nevertheless, these static and single‐purpose characteristics lack the ability to adjust to rapidly changing weather conditions, often leading to excessive cooling. To overcome this challenge, the emergence of dual‐mode smart flipping technologies has provided a pathway for dynamically adjusting the heating or cooling of objects in response to fluctuations in ambient temperature. First, the underlying principles of dual‐mode smart flipping are shown. Then the evolving materials and approaches of smart flipping are given an introduction to adapt to different environments under external stimuli, such as mechanical flipping, temperature, humidity, and so forth. Afterward, we present the recent applications of dual‐mode smart flipping materials and devices in personal thermal management, thermoelectric generation, energy‐saving buildings, and smart windows. Finally, the challenges and outlook of dual‐mode smart flipping are presented and future directions are identified.